1,3-Propanediamine → N-(3-aminopropyl)-6-chloro-1,2,3,4-tetrahydroacridin-9-amine

HRID 1821087Notes

Reaction equation

HRID 1821087 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](Cl)=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2.[NH2:17][CH2:18][CH2:19][CH2:20][NH2:21].C(O)CCCC.C(=O)(O)[O-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:17][CH2:18][CH2:19][CH2:20][NH2:21])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2

Participants

5

Reactant 4

HCID 4281,3-PropanediamineHCID 62761-PentanolHCID 2196646,9-Dichloro-1,2,3,4-tetrahydroacridineHCID 516892Sodium Bicarbonate

Product 1

HCID 23645224N-(3-aminopropyl)-6-chloro-1,2,3,4-tetrahydroacridin-9-amineYield 87%

Procedure

To a sealed tube was charged a mixture of 6,9-dichloro-1,2,3,4-tetrahydroacridine (1.0 g, 3.97 mmoL), 1,3-diaminopropane (1.67 mL, 19.83 mmoL) and 4 mL 1-pentanol. The mixture was heated to 160 degree Celsius for 24 h. After cooled down and saturated sodium bicarbonate was added, the mixture was extracted with dichloromethane three times. The combined extract was dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography on silica gel with 10-20% MeOH/CH2Cl2 (1% ammonium hydroxide) to give the desired product as brown oil (1.0 g, 87%).

Workup

  1. additionTo a sealed tube was charged
  2. temperatureThe mixture was heated to 160 degree Celsius for 24 h
  3. temperatureAfter cooled down
  4. extractionthe mixture was extracted with dichloromethane three times
  5. extractionThe combined extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by column chromatography on silica gel with 10-20% MeOH/CH2Cl2 (1% ammonium hydroxide)

Sources & evidence

ORD record
ord-2e3ba6e0ae544488bac4b34d3f5b7733
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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